Bioassay-directed isolation of quaternary benzylisoquinolines from Berberis integerrima with bactericidal activity against Brucella abortus
Abstract
Berberis integerrima Bonge. (Syn: Berberis densiflora Boiss. & Buhse) is a shrub widely distributed in Middle East and central part of Asia. An ethnobotanical study revealed that indigenous and tribal people in Iran use B. integerrima root decoction for treatment of brucellosis. Therefore, the aim of this study was bioassay directed isolation of antibacterial compounds from this plant based on their in vitro bactericidal activity against Brucella abortus. Briefly, the ethanol extract of B. integerrima was fractioned and subjected to preliminary antibacterial screening tests against Brucella. The more active fraction (Fr.3) was subjected to purification by repeated chromatography systems. Quaternary benzylisoquinoline alkaloids including columbamine, palmatine, berberine, and jatrorhizine were four main components identified in the selected active fraction. Except for berberine which is reported before, palmatine, columbamine and jatrorhizine are isolated for the first time from this plant. Anti-brucellosis properties of isolated compounds 1-4 were studied against B. abortus under different test conditions. In minimum inhibitory concentration (MIC) and minimum bactericidal concentration (MBC) results, jatrorhizine (4) showed more antibacterial activity with MIC and MBC of 0.78 and 1.56 μg/mL, respectively. In both agar well diffusion and disk diffusion ANOVA results showed that there were statistically significant differences between compounds 1-4 versus placebo in all of the tested concentration (P <0.001). In conclusion, all of four alkaloids showed potent antibacterial activity against B. abortus but jatrorhizine and columbamine with free hydroxyl group on C-3 or C-2 showed more activity than palmatine and berberine without any free hydroxyl group on their structures. The antibacterial effects of columbamine (15 μg/mL) and jatrorhizine (15 μg/mL) were comparative to streptomycin (10 μg/mL) as standard drug which candidate them for more pharmacological researches to find new antibacterial agents against brucellosis.
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Pappas G, Papadimitriou P, Akritidis N, Christou L, Tsianos EV. The new global map of human brucellosis. Lancet Infect Dis. 2006;6:91-99.
Franco MP, Mulder M, Gilman RH, Smits HL. Human brucellosis. Lancet Infect Dis. 2007;7:775-786.
Porte F, Naroeni A, Ouahrani-Bettache S, Liautard JP. Role of the Brucella suis lipopolysaccharide O antigen in phagosomal genesis and in inhibition of phagosome-lysosome fusion in murine macrophages. Infect Immun. 2003;71:1481-1490.
Skalsky K, Yahav D, Bishara J, Pitlik S, Leibovici L, Paul M. Treatment of human brucellosis: systematic review and meta-analysis of randomised controlled trials. BMJ. 2008;336:701-704.
Dizer U, Hayat L, Beker CM, Görenek L, Özgüven V, Pahsa A. The effect of the doxycycline-rifampicin and levamisole combination on lymphocyte subgroups and functions of phagocytic cells in patients with chronic brucellosis. Chemotherapy. 2005;51:27-31.
Pirbalouti AG. Medicinal plants used in Chaharmahal and Bakhtyari districts of Iran. Herba Polonica, 2009;55:69-77.
Ghasemi Pirbalouti A, Ghasemi MR, Momtaz H, Golparvar AR, Hamedi B, Shahgholian L. The effect of some of the Iranian medicinal plants on Brucella Abortus on In-vitro and In-vivo. J Herb Med. 2010;1:21-29.
Ashraf H, Heidari R, Nejati V. Antihyperglycemic and antihyperlipidemic effects of fruit aqueous extract of Berberis integerrima Bge. in streptozotocin-induced diabetic rats. Iran J Pharm Res. 2014;13:1313-1318.
Alemardan A, Asadi W, Rezaei M, Tabrizi L, Mohammadi S. Cultivation of Iranian seedless barberry (Berberis integerrima ‘Bidaneh’): A medicinal shrub. Ind Crops Prod. 2013;50:276-287.
Karimov A, Vinogradova VI, Shakirov R. Berberis alkaloids. XXII. Interbrinine and intebrimine-New alkaloids from Berberis integerrima. Chem Nat Compd. 1993;29:57-60.
Arayne MS, Sultana N, Bahadur SS. The berberis story: Berberis vulgaris in therapeutics. Pak J Pharm Sci. 2007;20:83-92.
Suau R, Rico R, López-Romero JM, Nájera F, Cuevas A. Isoquinoline alkaloids from Berberis vulgaris subsp. australis. Phytochemistry. 1998;49(8):2545-2549.
Reller LB, Weinstein M, Jorgensen JH, Ferraro MJ. Antimicrobial susceptibility testing: a review of general principles and contemporary practices. Clin Infect Dis. 2009;49:1749-1755.
Ayatollahi AM, Ghanadian M, Afsharypuor S, Siddiq S, Pour-Hosseini SM. Biological screening of Euphorbia aellenii. Iran J Pharm Res. 2010;9: 429-436.
Hsieh TJ, Chia YC, Wu YC, Chen CY. Chemical constituents from the stems of Mahonia japonica. J Chin Chem. 2004;51:443-446.
Boyanova L, Gergova G, Nikolov R, Derejian S, Lazarova E, Katsarov N, Mitov I, Krastev Z. Activity of Bulgarian propolis against 94 Helicobacter pylori strains in vitro by agar-well diffusion, agar dilution and disc diffusion methods.J Med Microbiol. 2005;54:481-483.
Li CY, Lu HJ, Lin CH, Wu TS. A rapid and simple determination of protoberberine alkaloids in cortex phellodendri by 1H-NMR and its application for quality control of commercial traditional Chinese medicine prescriptions. J Pharm Biomed Anal. 2006;40:173-178.
Leyva-Peralta MA, Robles-Zepeda RE, Garibay-Escobar A, Ruiz-Bustos E, Alvarez-Berber LP, Gálvez-Ruiz JC. In vitro anti-proliferative activity of Argemone gracilenta and identification of some active components. Complement Altern Med. 2015;15:13-19.
Alimirzaee P, Gohari AR, Hajiaghaee R, Mirzaee S, Jamalifar H, Monsef Esfahani HR, et al. 1‐methyl malate from Berberis integerrima fruits enhances the antibacterial activity of ampicillin against Staphylococcus aureus. Phytother Res. 2009;23: 797-800.
Villinski J, Dumas E, Chai HB, Pezzuto J, Angerhofer C, Gafner S. Antibacterial activity and alkaloid content of Berberis thunbergii, Berberis vulgaris and Hydrastis canadensis. Pharm Biol. 2003;41:551-557.
Irshad AH, Pervaiz AH, Abrar YB, Fahelboum I, Awen BZ. Antibacterial activity of Berberis lycium root extract. Trakia J Sci. 2013;1:88-90.
Singh M, Srivastava S, Rawat AK. Antimicrobial activities of Indian Berberis species. Fitoterapia. 2007;78(7-8):574-576.
Paulo MD, Barbosa-Filho J, Lima EO, Maia RF, de Cassia R, Barbosa BB, et al. Antimicrobial activity of benzylisoquinoline alkaloids from Annona salzmanii DC. J Ethnopharmacol. 1992;36:39-41.
Villar A, Mares M, Rios JL, Canton E, Gobernado M. Antimicrobial activity of benzylisoquinoline alkaloids. Die Pharmazie. 1987;42:248-250.
Bandyopadhyay S, Patra PH, Mahanti A, Mondal DK, Dandapat P, Bandyopadhyay S, et al. Potential antibacterial activity of berberine against multi drug resistant enterovirulent Escherichia coli isolated from
yaks (Poephagus grunniens) with haemorrhagic diarrhoea. Asian Pac J Trop Dis. 2013;6:315-319.
Iwasa K, Nishiyama Y, Ichimaru M, Moriyasu M, Kim HS, Wataya Y, et al. Structure-activity relationships of quaternary protoberberine alkaloids having an antimalarial activity. Eur J Med Chem. 1999;34:1077-1083.
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